
25. Eternity of Pain
The Cleveland Browns have been around since the ’40s yet have never won a Super bowl. In fact, since 1999 they somehow managed to cause an eternity of pain for their fanbase. So much so that when analysts asked one fan what moment left him embarrassed, he had an emphatic response. “That time between 1999-2018 haha remember that time guys,” he replied. A lot of things have gone wrong in Cleveland.

Now, we could focus on their winless season in 2017 because this was literally rock-bottom for the franchise. But in truth, they’ve had a very rough time of it, with just three winning seasons between 1999 and 2020. Finally, they snapped their playoff drought in the latter year, but as this fan revealed, it’s been a tough go to be a Browns fan. They have embarrassed their fans and the city so often.